Aromatic systems like phenol, diphenol, cyano benzene, chloro benzene, aniline etc shows effective π-π stacking interactions, long range van der Waals forces; ion-π interactions etc. and these forces of interactions play an crucial role in the stability of stacked π-dimeric system. On the other hand, substituents and conformational change in the stacked dimmers of aromatic system may also change the stability of different stacked dimers. In this current study, stacked phenolic dimmers (both phenol and diphenol) have been taken for investigation of the stacking π-π interaction. But, the stacking interactions are also greatly affected by the conformational change with internal rotation (i.e. dihedral angle, φ) between the stacked dimers. It is generally accepted that larger basis sets are required for the highly accurate calculation of interaction energies for any stacked aromatic models. But, it has recently been reported that M062X/6-311++G(d,p) basis set is effectively better than that of B3LYP/6-311++G(d,p) for determining the interaction energies for any kind of long range interaction in aromatic systems. Therefore, all the calculations were carried out by using M062X/6-311++G(d,p) basis set. However, in most of the cases the calculated π-π stacking interaction energies show almost same result for both DFT and ab initio methods.